Английская Википедия:25-NB

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Шаблон:Short description

Файл:25-NB-structure-general.png
General structure of 25-NB derivatives, where R is usually 2,5-dimethoxy-4-(alkyl or halogen), R1 is usually H but rarely methyl, and Cyc is usually 2-substituted phenyl but can be other heterocycles.

The 25-NB (25x-NBx) series, sometimes alternatively referred to as the NBOMe compounds, is a family of serotonergic psychedelics.[1] They are substituted phenethylamines and were derived from the 2C family.[1] They act as selective agonists of the serotonin 5-HT2A receptor.[2][3][4][5][6][7][8] The 25-NB family is unique relative to other classes of psychedelics in that they are, generally speaking, extremely potent and relatively selective for the 5-HT2A receptor.[1] Use of NBOMe series drugs has caused many deaths and hospitalisations since the drugs popularisation in the 2010s. This is primarily due to their high potency, unpredictable pharmacokinetics, and sellers passing off the compounds in the series as LSD.[9]

Toxicity and harm potential

NBOMe compounds are often associated with life-threatening toxicity and death.[10][11] Studies on NBOMe family of compounds demonstrated that the substance exhibit neurotoxic and cardiotoxic activity.[12] Reports of autonomic dysfunction remains prevalent with NBOMe compounds, with most individuals experiencing sympathomimetic toxicity such as vasoconstriction, hypertension and tachycardia in addition to hallucinations.[13][14][15][16][17] Other symptoms of toxidrome of include agitation or aggression, seizure, hyperthermia, diaphoresis, hypertonia, rhabdomyolysis, and death.[13][17][11] Researchers report that NBOMe intoxication frequently display signs of serotonin syndrome.[18] The likelihood of seizure is higher in NBOMes compared to other psychedelics.[12]

NBOMe and NBOHs are regularly sold as LSD in blotter papers,[11][19] which have a bitter taste and different safety profiles.[13][10] Despite high potency, recreational doses of LSD have only produced low incidents of acute toxicity.[10] Fatalities involved in NBOMe intoxication suggest that a significant number of individuals ingested the substance which they believed was LSD,[15] and researchers report that "users familiar with LSD may have a false sense of security when ingesting NBOMe inadvertently".[13] While most fatalities are due to the physical effects of the drug, there have also been reports of death due to self-harm and suicide under the influence of the substance.[20][21][13]

Given limited documentation of NBOMe consumption, the long-term effects of the substance remain unknown.[13] NBOMe compounds are not active orally,Шаблон:Efn and are usually taken sublingually.[1]Шаблон:Rp When NBOMes are administered sublingually, numbness of the tongue and mouth followed by a metallic chemical taste was observed, and researchers describe this physical side effect as one of the main discriminants between NBOMe compounds and LSD.[22][23][24]

Neurotoxic and cardiotoxic actions

Many of the NBOMe compounds have high potency agonist activity at additional 5-HT receptors and prolonged activation of 5-HT2B can cause cardiac valvulopathy in high doses and chronic use.[11][16] 5-HT2B receptors have been strongly implicated in causing drug-induced valvular heart disease.[25][26][27] The high affinity of NBOMe compounds for adrenergic α1 receptor has been reported to contribute to the stimulant-type cardiovascular effects.[16]

In vitro studies, 25C-NBOMe has been shown to exhibit cytotoxicity on neuronal cell lines SH-SY5Y, PC12, and SN471, and the compound was more potent than methamphetamine at reducing the visibility of the respective cells; the neurotoxicity of the compound involves activation of MAPK/ERK cascade and inhibition of Akt/PKB signaling pathway.[12] 25C-NBOMe, including the other derivative 25D-NBOMe, reduced the visibility of cardiomyocytes H9c2 cells, and both substances downregulated expression level of p21 (CDC24/RAC)-activated kinase 1 (PAK1), an enzyme with documented cardiac protective effects.[12]

Preliminary studies on 25C-NBOMe have shown that the substance is toxic to development, heart health, and brain health in zebrafish, rats, and Artemia salina, a common organism for studying potential drug effects on humans, but more research is needed on the topic, the dosages, and if the toxicology results apply to humans. Researchers of the study also recommended further investigation of the drug's potential in damaging pregnant women and their fetus due to the substance's damaging effects to development.[28][29]

Emergency treatment

At present, there are no specific antidotes for NBOMes, and all acute intoxication is managed by symptomatic treatments, such as administration of benzodiazepines, antipsychotic drugs, and antiarrhythmic agents, such as beta blockers; some emergency interventions are intended to specifically treat rhabdomyolysis, which may lead to critical complications such as metabolic acidosis and acute kidney injury.[12]

Chemical structure

The 25-NB compounds are mostly N-benzylphenethylamines,[1][30] though in some cases the phenyl ring of the N-benzyl group is replaced by other heterocycles such as thiophene, pyridine, furan, tetrahydrofuran, benzodioxole or naphthalene, among others.[31][32]

Generally speaking, they have methoxy groups at the 2 and 5 positions of the phenyl ring, a substitution such as a halogen or alkyl group at the 4 position of the phenyl ring, and a methoxy or other substitution (e.g., hydroxyl, fluoro) at the 2 position of the N-benzyl ring.[1] More rarely, other substitution patterns may be present [33][34] (see e.g. NBOMe-mescaline, 25G-NBOMe, 2CBFly-NBOMe, 25C-NB3OMe). They differ from the 2C series by the presence of the N-benzyl moiety.[1]

Rarely an alpha-methyl group is present making them N-benzyl amphetamines rather than N-benzyl phenethylamines, but this greatly reduces potency and activity. However in some cases where a side chain methyl group is cyclised back to the ring (e.g. in 2CBCB-NBOMe) or links the two alpha positions (e.g. in DMBMPP), this can improve selectivity for the 5-HT2A receptor subtype.[35]

List of 25-NB derivatives

Файл:2C-I-NBOMe-skeletal.svg
25I-NBOMe, the most well-known 25-NB derivative

This list includes notable compounds representative of most of the structural variations that have been explored in this series, but is by no means exhaustive. Many derivatives invented for scientific study into the structure-activity relationships of 5-HT2 receptor agonists have never appeared as designer drugs, while conversely some derivatives that have appeared as designer drugs are structurally novel and of unknown pharmacological activity (e.g. C30-NBOMe, 5-APB-NBOMe).

Chemical structure Common name Chemical name CAS number R R1 Cyc
Файл:25B-NB structure.png 25B-NB N-benzyl-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 155639-26-2 2,5-dimethoxy-4-bromo H phenyl
Файл:25C-NB structure.png 25C-NB N-benzyl-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1391487-65-2 2,5-dimethoxy-4-chloro H phenyl
Файл:25I-NB structure.png 25I-NB N-benzyl-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-18-5 2,5-dimethoxy-4-iodo H phenyl
Файл:25I-NMeTh structure.png 25I-NMeTh N-[(thiophen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391499-03-8 2,5-dimethoxy-4-iodo H thiophen-2-yl
Файл:25B-NMePyr structure.png 25B-NMePyr N-[(pyridin-2-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391499-21-0 2,5-dimethoxy-4-bromo H pyridin-2-yl
Файл:25I-NMeFur structure.png 25I-NMeFur N-[(furan-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391498-93-3 2,5-dimethoxy-4-iodo H furan-2-yl
Файл:25I-NMeTHF structure.png 25I-NMeTHF N-[(tetrahydrofuran-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 2,5-dimethoxy-4-iodo H tetrahydrofuran-2-yl
Файл:25B-NBF.svg 25B-NBF N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1539266-17-5 2,5-dimethoxy-4-bromo H 2-fluorophenyl
Файл:25B-NBOH structure.png 25B-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1335331-46-8 2,5-dimethoxy-4-bromo H 2-hydroxyphenyl
Файл:2C-B-NBOMe-skeletal.svg 25B-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1026511-90-9 2,5-dimethoxy-4-bromo H 2-methoxyphenyl
Файл:25B-NB23DM structure.png 25B-NB23DM N-(2,3-dimethoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391493-68-7 2,5-dimethoxy-4-bromo H 2,3-dimethoxyphenyl
Файл:25B-NB25DM structure.png 25B-NB25DM N-(2,5-dimethoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 2,5-dimethoxy-4-bromo H 2,5-dimethoxyphenyl
Файл:25B-NMe7BF structure.png 25B-NMe7BF N-[(benzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391492-46-8 2,5-dimethoxy-4-bromo H benzofuran-7-yl
Файл:25B-NMe7DHBF structure.png 25B-NMe7DHBF N-[(2,3-dihydrobenzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391492-40-2 2,5-dimethoxy-4-bromo H 2,3-dihydrobenzofuran-7-yl
Файл:25B-NMe7BT structure.png 25B-NMe7BT N-[(benzothiophen-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391492-59-3 2,5-dimethoxy-4-bromo H benzothiophen-7-yl
Файл:25B-NMe7Box structure.png 25B-NMe7Box N-[(benzoxazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391498-73-9 2,5-dimethoxy-4-bromo H benzoxazol-7-yl
Файл:25B-NMe7Ind structure.png 25B-NMe7Ind N-[(indol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391498-28-4 2,5-dimethoxy-4-bromo H indol-7-yl
Файл:25B-NMe7Indz structure.png 25B-NMe7Indz N-[(indazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391498-43-3 2,5-dimethoxy-4-bromo H indazol-7-yl
Файл:25B-NMe7Bim structure.png 25B-NMe7Bim N-[(benzimidazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1391498-62-6 2,5-dimethoxy-4-bromo H benzimidazol-7-yl
Файл:FECIMBI-36 structure.png FECIMBI-36 N-[(2-fluoroethoxy)benzyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 2,5-dimethoxy-4-bromo H 2-(2-fluoroethoxy)phenyl
Файл:DOB-NBOMe structure.png DOB-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane 2,5-dimethoxy-4-bromo methyl 2-methoxyphenyl
Файл:25C-NB3OMe.svg 25C-NB3OMe N-(3-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1566571-34-3 2,5-dimethoxy-4-chloro H 3-methoxyphenyl
Файл:25C-NB4OMe.svg 25C-NB4OMe N-(4-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1566571-35-4 2,5-dimethoxy-4-chloro H 4-methoxyphenyl
Файл:C30-NBOMe structure.png C30-NBOMe N-(3,4,5-trimethoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1445574-98-0 2,5-dimethoxy-4-chloro H 3,4,5-trimethoxyphenyl
Файл:25C-NBF.svg 25C-NBF N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1539266-21-1 2,5-dimethoxy-4-chloro H 2-fluorophenyl
Файл:25C-NBCl structure.png 25C-NBCl N-(2-chlorobenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 2,5-dimethoxy-4-chloro H 2-chlorophenyl
Файл:NBOH-2CC structure.png 25C-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1391488-16-6 2,5-dimethoxy-4-chloro H 2-hydroxyphenyl
Файл:2C-C-NBOMe-skeletal.svg 25C-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1227608-02-7 2,5-dimethoxy-4-chloro H 2-methoxyphenyl
Файл:25C-NBOEt structure.png 25C-NBOEt N-(2-ethoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 2,5-dimethoxy-4-chloro H 2-ethoxyphenyl
Файл:25C-NBOiPr structure.png 25C-NBOiPr N-(2-isopropoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 2,5-dimethoxy-4-chloro H 2-isopropoxyphenyl
Файл:25F-NBOMe structure.png 25F-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-fluorophenyl)-2-aminoethane 1373917-84-0 2,5-dimethoxy-4-fluoro H 2-methoxyphenyl
Файл:NBOH-2CCN structure.png 25CN-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane 1539266-32-4 2,5-dimethoxy-4-cyano H 2-hydroxyphenyl
Файл:25CN-NBOMe.svg 25CN-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane 1354632-16-8 2,5-dimethoxy-4-cyano H 2-methoxyphenyl
Файл:25D-NBOMe2DACS.svg 25D-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane 1354632-02-2 2,5-dimethoxy-4-methyl H 2-methoxyphenyl
Файл:25D-NBOH structure.png 25D-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane 1391488-44-0 2,5-dimethoxy-4-methyl H 2-hydroxyphenyl
Файл:2C-E-NBOMe 2DACS.svg 25E-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-ethylphenyl)-2-aminoethane 1354632-14-6 2,5-dimethoxy-4-ethyl H 2-methoxyphenyl
Файл:25E-NBOH structure.png 25E-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-ethylphenyl)-2-aminoethane 1391489-79-4 2,5-dimethoxy-4-ethyl H 2-hydroxyphenyl
Файл:25G-NBOMe.svg 25G-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-3,4-dimethylphenyl)-2-aminoethane 1354632-65-7 2,5-dimethoxy-3,4-dimethyl H 2-methoxyphenyl
Файл:25H-NBOMe.svg 25H-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxyphenyl)-2-aminoethane 1566571-52-5 2,5-dimethoxy H 2-methoxyphenyl
Файл:25I-NB34MD.svg 25I-NB34MD N-(3,4-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391497-81-6 2,5-dimethoxy-4-iodo H 3,4-methylenedioxyphenyl
Файл:25I-NB3OMe.svg 25I-NB3OMe N-(3-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1566571-40-1 2,5-dimethoxy-4-iodo H 3-methoxyphenyl
Файл:25I-NB4OMe.svg 25I-NB4OMe N-(4-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1566571-41-2 2,5-dimethoxy-4-iodo H 4-methoxyphenyl
Файл:25i-NBF.svg 25I-NBF N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-21-0 2,5-dimethoxy-4-iodo H 2-fluorophenyl
Файл:25I-NBBr structure.png 25I-NBBr N-(2-bromobenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1648649-98-2 2,5-dimethoxy-4-iodo H 2-bromophenyl
Файл:25I-NBTFM structure.png 25I-NBTFM N-[2-(trifluoromethyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 2,5-dimethoxy-4-iodo H 2-(trifluoromethyl)phenyl
Файл:25I-NBMD.svg 25I-NBMD N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-25-4 2,5-dimethoxy-4-iodo H 2,3-methylenedioxyphenyl
Файл:25B-NBMD structure.png 25B-NBMD N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane 1354632-19-1 2,5-dimethoxy-4-bromo H 2,3-methylenedioxyphenyl
Файл:25C-NBMD structure.png 25C-NBMD N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 1373879-26-5 2,5-dimethoxy-4-chloro H 2,3-methylenedioxyphenyl
Файл:25D-NBMD structure.png 25D-NBMD N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane 1391488-97-3 2,5-dimethoxy-4-methyl H 2,3-methylenedioxyphenyl
Файл:2C-I-NBOH-skeletal.svg 25I-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-20-9 2,5-dimethoxy-4-iodo H 2-hydroxyphenyl
Файл:2C-I-NBOMe-skeletal.svg 25I-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 919797-19-6 2,5-dimethoxy-4-iodo H 2-methoxyphenyl
Файл:DOI-NBOMe structure.png DOI-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane 2,5-dimethoxy-4-iodo methyl 2-methoxyphenyl
Файл:25I-NBMeOH structure.png 25I-NBMeOH N-[2-(hydroxymethyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391494-71-5 2,5-dimethoxy-4-iodo H 2-(hydroxymethyl)phenyl
Файл:25I-NBAm structure.png 25I-NBAm N-[2-(carbamoyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1391494-85-1 2,5-dimethoxy-4-iodo H 2-(carbamoyl)phenyl
Файл:25I-NMe7DHBF structure.png 25I-NMe7DHBF N-[(2,3-dihydrobenzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 2,5-dimethoxy-4-iodo H 2,3-dihydrobenzofuran-7-yl
Файл:25I-N2Nap1OH structure.png 25I-N2Nap1OH N-[(1-hydroxynaphthalen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 2,5-dimethoxy-4-iodo H 1-hydroxynaphthalen-2-yl
Файл:25I-N3MT2M structure.png 25I-N3MT2M N-[(3-methoxythiophen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1354632-66-8 2,5-dimethoxy-4-iodo H 3-methoxythiophen-2-yl
Файл:25I-N4MT3M structure.png 25I-N4MT3M N-[(4-methoxythiophen-3-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane 1354632-73-7 2,5-dimethoxy-4-iodo H 4-methoxythiophen-3-yl
Файл:25iP-NBOMe.svg 25iP-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-isopropylphenyl)-2-aminoethane 1391487-83-4 2,5-dimethoxy-4-isopropyl H 2-methoxyphenyl
Файл:25N-NBOMe structure 300px.png 25N-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 1354632-03-3 2,5-dimethoxy-4-nitro H 2-methoxyphenyl
Файл:25N-NBOEt structure.png 25N-NBOEt [36] N-(2-ethoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H 2-ethoxyphenyl
Файл:25N-NB-2-OH-3-Me structure.png 25N-NB-2-OH-3-Me N-(2-hydroxy-3-methylbenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H 2-hydroxy-3-methylphenyl
Файл:25N-NBOCF2H structure.png 25N-NBOCF2H N-(2-difluoromethoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H 2-difluoromethoxyphenyl
Файл:25N-NBPh structure.png 25N-NBPh[37] N-[(2-phenyl)benzyl]-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H o-biphenyl
Файл:25N-N1-Nap structure.png 25N-N1-Nap N-[(naphthalen-1-yl)methyl]-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane 2,5-dimethoxy-4-nitro H 1-naphthyl
Файл:25P-NBOMe2DACS.svg 25P-NBOMe N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-propylphenyl)-2-aminoethane 1391489-07-8 2,5-dimethoxy-4-propyl H 2-methoxyphenyl
Файл:25P-NBOH structure.png 25P-NBOH N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-propylphenyl)-2-aminoethane 1391490-34-8 2,5-dimethoxy-4-propyl H 2-hydroxyphenyl
Файл:2C-TFM-NBOMe.svg 25TFM-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(trifluoromethyl)phenyl]-2-aminoethane 1027161-33-6 2,5-dimethoxy-4-(trifluoromethyl) H 2-methoxyphenyl
Файл:25O-NBcPr structure.png 25O-NBcP N-(2-cyclopropylbenzyl)-1-(2,4,5-trimethoxyphenyl)-2-aminoethane 2,4,5-trimethoxy H 2-cyclopropylphenyl
Файл:25T-NBOMe structure.png 25T-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(methylthio)phenyl]-2-aminoethane 1539266-47-1 2,5-dimethoxy-4-(methylthio) H 2-methoxyphenyl
Файл:25T2-NBOMe structure.png 25T2-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(ethylthio)phenyl]-2-aminoethane 1539266-51-7 2,5-dimethoxy-4-(ethylthio) H 2-methoxyphenyl
Файл:25T4-NBOMe structure.png 25T4-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(isopropylthio)phenyl]-2-aminoethane 1354632-17-9 2,5-dimethoxy-4-(isopropylthio) H 2-methoxyphenyl
Файл:25T7-NBOMe structure.png 25T7-NBOMe N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(propylthio)phenyl]-2-aminoethane 1539266-55-1 2,5-dimethoxy-4-(propylthio) H 2-methoxyphenyl
Файл:25T7-NBOH structure.png 25T7-NBOH N-(2-hydroxybenzyl)-1-[2,5-dimethoxy-4-(propylthio)phenyl]-2-aminoethane 1354632-41-9 2,5-dimethoxy-4-(propylthio) H 2-hydroxyphenyl
Файл:NBOMe-2C-AM structure.png 25AM-NBOMe [38] N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-pentylphenyl]-2-aminoethane 2,5-dimethoxy-4-(n-pentyl) H 2-methoxyphenyl
Файл:NBOMe-mescaline-molecule.png NBOMe-mescaline N-(2-methoxybenzyl)-1-(3,4,5-trimethoxyphenyl)-2-aminoethane 1354632-01-1 3,4,5-trimethoxy H 2-methoxyphenyl
Файл:Escaline-NBOMe structure.png NBOMe-escaline N-(2-methoxybenzyl)-1-(3,5-dimethoxy-4-ethoxyphenyl)-2-aminoethane 3,5-dimethoxy-4-ethoxy H 2-methoxyphenyl
Файл:NBOMe-thiobuscaline structure.png NBOMe-thiobuscaline N-(2-methoxybenzyl)-1-(3,5-dimethoxy-4-butylthiophenyl)-2-aminoethane 3,5-dimethoxy-4-(n-butylthio) H 2-methoxyphenyl
Файл:MDPEA-NBOMe structure.png MDPEA-NBOMe N-(2-methoxybenzyl)-1-(3,4-methylenedioxyphenyl)-2-aminoethane 3,4-methylenedioxy H 2-methoxyphenyl
Файл:2C2-NBOMe structure.png 2C2-NBOMe N-(2-methoxybenzyl)-1-(2-methoxy-4,5-methylenedioxyphenyl)-2-aminoethane 2-methoxy-4,5-methylenedioxy H 2-methoxyphenyl
Файл:MDBZ.svg MDBZ N-benzyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane 65033-29-6 3,4-methylenedioxy methyl phenyl
Файл:Clobenzorex structure.svg Clobenzorex N-(2-chlorobenzyl)-1-phenyl-2-aminopropane 13364-32-4 H methyl 2-chlorophenyl
Файл:4EA-NBOMe structure.png 4-EA-NBOMe N-(2-methoxybenzyl)-1-(4-ethylphenyl)-2-aminopropane 4-ethyl methyl 2-methoxyphenyl
Файл:5APB-NBOMe structure.png 5-APB-NBOMe N-(2-methoxybenzyl)-1-(benzofuran-5-yl)-2-aminopropane benzofuran-5-yl instead of phenyl methyl 2-methoxyphenyl

Similar compounds with related structures are also known including;

Chemical structure Common name Chemical name CAS number
Файл:25B-N1POMe structure.png 25B-N1POMe N-[1-(2-methoxyphenyl)ethyl]-2,5-dimethoxy-4-bromophenethylamine 1335331-49-1 (R)
1335331-51-5 (S)
Файл:2CB-AN structure.png 2C-B-AN [39][40] 2-phenyl-2-[2-(2,5-dimethoxy-4-bromophenyl)ethylamino]acetonitrile
Файл:25B-N(BOMe)2 structure.png 25B-N(BOMe)2 2-(4-Bromo-2,5-dimethoxyphenyl)-N,N-bis(2-methoxybenzyl)ethan-1-amine
Файл:2CBCB-NBOMe-skeletal.svg 2CBCB-NBOMe N-[(3-bromo-2,5-dimethoxy-bicyclo[4,2,0]octa-1,3,5-trien-7-yl)methyl]-1-(2-methoxyphenyl)methanamine 1354634-09-5
Файл:2CBFly-NBOMe.svg 2CBFly-NBOMe N-(2-methoxybenzyl)-1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane 1335331-42-4
Файл:2CB-DRAGONFLY-NBOH structure.png 2C-B-DRAGONFLY-NBOH N-(2-hydroxybenzyl)-1-(8-bromobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane 1335331-45-7
Файл:2CBFLY-NB2EtO5Cl structure.png 2C-B-FLY-NB2EtO5Cl [41] N-(2-ethoxy-5-chlorobenzyl)-1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane
Файл:SS9b structure.png DMBMPP (S,S)-2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine 1391499-52-7
Файл:25B-NAcPip structure.png 25B-NAcPip 2-{[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]amino}-1-(piperidin-1-yl)ethanone
Файл:ZDCM-04 structure.png ZDCM-04 1,3-dimethyl-7-{2-[1-(2,5-dimethoxy-4-chlorophenyl)propan-2-ylamino]ethyl}purine-2,6-dione
Файл:RH-34 structure.png RH-34 3-[2-(2-methoxybenzylamino)ethyl]-1H-quinazoline-2,4-dione 1028307-48-3
Файл:5MT-NBOMe structure.png 5-MeO-T-NBOMe[42] N-(2-methoxybenzyl)-5-methoxytryptamine 1335331-37-7
Файл:5MT-NB3OMe structure.png 5MT-NB3OMe N-(3-methoxybenzyl)-5-methoxytryptamine 1648553-42-7

Legality

United Kingdom

A large number of substances in the 25-NB class are Class A drugs in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971[43] or are otherwise covered by the Psychoactive Substances Act 2016.[44]

See also

Notes

Шаблон:Notelist

External links

References

Шаблон:Reflist

Шаблон:Hallucinogens Шаблон:Serotonin receptor modulators Шаблон:Phenethylamines

Партнерские ресурсы
Криптовалюты
Магазины
Хостинг
Разное

  1. ↑ 1,0 1,1 1,2 1,3 1,4 1,5 1,6 Шаблон:Cite book
  2. ↑ Шаблон:Cite journal
  3. ↑ Шаблон:Cite thesis
  4. ↑ Шаблон:Cite thesis
  5. ↑ Шаблон:Cite thesis
  6. ↑ Шаблон:Cite journal
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  8. ↑ Шаблон:Cite journal
  9. ↑ Шаблон:Cite journal
  10. ↑ 10,0 10,1 10,2 Шаблон:Cite journal
  11. ↑ 11,0 11,1 11,2 11,3 Шаблон:Cite journal
  12. ↑ 12,0 12,1 12,2 12,3 12,4 Шаблон:Cite journal
  13. ↑ 13,0 13,1 13,2 13,3 13,4 13,5 Шаблон:Cite journal
  14. ↑ Шаблон:Cite journal
  15. ↑ 15,0 15,1 Шаблон:Cite journal
  16. ↑ 16,0 16,1 16,2 Шаблон:Cite journal
  17. ↑ 17,0 17,1 Шаблон:Cite journal
  18. ↑ Шаблон:Cite journal
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  20. ↑ Шаблон:Cite journal
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  35. ↑ Шаблон:Cite journal
  36. ↑ Wallach J, et al. Selective, Partial and Arrestin-Biased 5-HT2A Agonists with Utility in Various Disorders. Patent WO 2022/241006
  37. ↑ Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD. Identification of 5-HT2A Receptor Signaling Pathways Responsible for Psychedelic Potential. bioRxiv 2023 Jul 31:2023.07.29.551106. Шаблон:Doi Шаблон:PMID
  38. ↑ Kruegel AC. Phenalkylamines and Methods of Making and Using the Same. Patent WO 2022/192781
  39. ↑ Шаблон:Cite book
  40. ↑ Шаблон:Cite journal
  41. ↑ Шаблон:Cite journal
  42. ↑ Шаблон:Cite journal
  43. ↑ Шаблон:Cite web
  44. ↑ Шаблон:Cite web
Источник — http://wikihandbk.com/ruwiki/index.php?title=Английская_Википедия:25-NB&oldid=12840609